CALYCANTHINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26N4
Molecular Weight	346.4686
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC[C@@]23[C@@H]4NC5=C(C=CC=C5)[C@]2(CCN4C)[C@@H]1NC6=CC=CC=C36

InChI

InChIKey=XSYCDVWYEVUDKQ-GXRSIYKFSA-N

InChI=1S/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21-,22-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783 | https://www.henriettes-herb.com/eclectic/usdisp/calycanthus.html | https://www.sciencedirect.com/science/article/pii/S0095955315305564

Calycanthine is the principal alkaloid of the family Calycanthaceae. Calycanthine is a central nervous system toxin, causing convulsions in animals. Calycanthine may mediate its convulsant action predominantly by inhibiting the release of the inhibitory neurotransmitter GABA as a result of interactions with L-type Ca(2+) channels and by inhibiting GABA-mediated chloride currents at GABA(A) receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
gamma-aminobutyric acid secretion 1 Target ID: GO:0014051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783	Inhibitor 8297
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783	Blocker 537	42.0 µM [IC50]
GABA-A receptor; alpha-1/beta-2/gamma-2 27 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831783	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine.	2007	17415735
Antifungal activity of alkaloids from the seeds of Chimonanthus praecox.	2009 Jun	19551726

Patents

Sample Use Guides

In Vivo Use Guide

Median lethal dose of calycanthine in rodents: 43.79 mg/kg for mice, 17.16 mg/kg for rats

Route of Administration: Intravenous

In Vitro Use Guide

Calycanthine hydrochloride (10 uM), which did not alter nervous conduction in pre- and post-synaptic fibers, significantly reduced the efficacy of the synaptic transmission in giant axons of the cockroach (Periplaneta americana).

Name

Type

Language

CALYCANTHINE

Common Name

English

(4BS,5R,10BS,11R)-5,6,11,12-TETRAHYDRO-13,18-DIMETHYL-5,10B:11,4B-BIS(IMINOETHANO)-DIBENZO(C,H)(2,6)NAPHTHYRIDINE

Systematic Name

English

D-CALYCANTHINE

Common Name

English

(+)-CALYCANTHINE

Common Name

English

NSC-99016

Code

English

CALYCANTHINE [MI]

Common Name

English

5,10B:11,4B-BIS(IMINOETHANO)DIBENZO(C,H)(2,6)NAPHTHYRIDINE, 5,6,11,12-TETRAHYDRO-13,18-DIMETHYL-, (4BS,5R,10BS,11R)-

Systematic Name

English

Code System Code Type Description

CHEBI

3333